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Winchester, VA 55+ active adult communities & homes for sale

258 homes near Winchester

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5 rating (1 reviews) Willow Lawn Cottages
$300Ks
Willow Lawn Cottages, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2004 | 120 homes
Cross Creek Village
$300Ks - $400Ks
Cross Creek Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 90 homes
The Village at Harvest Ri...
$500Ks - $600Ks
The Village at Harvest Ri..., Winchester, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 82 homes
Woodbrook Village
$300Ks
Woodbrook Village, Winchester, VA
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 81 homes
Cottage Glen
$400Ks
Cottage Glen, Winchester, VA
New and Resale | Age-targeted | Built 2018 - present | 25 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Abrams Chase
$500Ks
Abrams Chase, Winchester, VA
New Construction | 55+ age-restricted | Built 2020 - present | 13 homes
5 rating (3 reviews) Heritage Hunt
$400Ks - $800Ks
Heritage Hunt, Gainesville, VA
Resale Only | 55+ age-restricted | Built 1998 - 2009 | 1,863 homes
2 rating (1 reviews) Birchwood at Brambleton
$400Ks - $1Ms
Birchwood at Brambleton, Ashburn, VA
New and Resale | 55+ age-restricted | Built 2016 - present | 1,502 homes
5 rating (2 reviews) Potomac Green
$700Ks - $800Ks
Potomac Green, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2005 - 2016 | 1,400 homes
5 rating (31 reviews) Lansdowne Woods of Virgin...
$300Ks - $400Ks
Lansdowne Woods of Virgin..., Lansdowne, VA
Resale Only | 55+ age-restricted | Built 1998 - 2017 | 1,200 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Penn National
$200Ks - $600Ks
Penn National, Fayetteville, PA
New and Resale | Age-targeted | Built 1968 - present | 1,100 homes
3.1 rating (7 reviews) Celebrate
$300Ks - $600Ks
Celebrate, Fredericksburg, VA
New and Resale | 55+ age-restricted | Built 2008 - present | 1,100 homes
5 rating (2 reviews) Trilogy® at Lake Frederic...
$400Ks - $1Ms
Trilogy® at Lake Frederic..., Lake Frederick, VA
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
5 rating (1 reviews) Regency at Dominion Valle...
$400Ks - $800Ks
Regency at Dominion Valle..., Haymarket, VA
Resale Only | 55+ age-restricted | Built 2001 - 2017 | 855 homes
5 rating (1 reviews) Four Seasons at Historic ...
$600Ks
Four Seasons at Historic ..., Dumfries, VA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 801 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
4.4 rating (5 reviews) Virginia Heritage at Lee'...
$400Ks - $600Ks
Virginia Heritage at Lee'..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2005 - 2021 | 795 homes
4.3 rating (3 reviews) Falls Run
$300Ks - $500Ks
Falls Run, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 781 homes
The Woodlands of Urbana
$600Ks
The Woodlands of Urbana, Urbana, MD
New Construction | 55+ age-restricted | Built 2019 - present | 565 homes
5 rating (1 reviews) Crestwood Village
$300Ks
Crestwood Village, Frederick, MD
Resale Only | 55+ age-restricted | Built 1979 - 1999 | 550 homes
Carter's Mill
$400Ks - $700Ks
Carter's Mill, Haymarket, VA
New Construction | 55+ age-restricted | Built 2020 - present | 480 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
3 rating (2 reviews) Dunbarton
$600Ks
Dunbarton, Bristow, VA
Resale Only | 55+ age-restricted | Built 2000 - 2009 | 479 homes
Montebello
$600Ks - $1Ms
Montebello, Sterling, VA
New and Resale | 55+ age-restricted | Built 2022 - present | 450 homes
Twin Lake Villas
$300Ks - $400Ks
Twin Lake Villas, Locust Grove, VA
New Construction | 55+ age-restricted | Built 2021 - present | 340 homes
Spring Hill
$500Ks - $800Ks
Spring Hill, Lorton, VA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 282 homes
Four Seasons at Charlotte...
$400Ks - $500Ks
Four Seasons at Charlotte..., Ruckersville, VA
Resale Only | 55+ age-restricted | Built 2005 - present | 275 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
ThreeOaksâ„¢
$400Ks - $800Ks
ThreeOaksâ„¢, Culpeper, VA
New Construction | 55+ age-restricted | Built 2024 - present | 268 homes
Regency at Ashburn
$800Ks - $900Ks
Regency at Ashburn, Ashburn, VA
Resale Only | 55+ age-restricted | Built 2013 - 2020 | 268 homes
Emerald Pointe
$300Ks - $400Ks
Emerald Pointe, Hagerstown, MD
New and Resale | 55+ age-restricted | Built 2008 - present | 250 homes
River Ridge
$500Ks - $700Ks
River Ridge, Woodbridge, VA
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 238 homes
Signature Club at Greenvi...
$400Ks - $900Ks
Signature Club at Greenvi..., New Market, MD
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 233 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Regency at Chancellorsvil...
$400Ks
Regency at Chancellorsvil..., Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 2004 - 2019 | 225 homes
The Retreat at Poland Hil...
$700Ks - $900Ks
The Retreat at Poland Hil..., Chantilly, VA
Resale Only | 55+ age-restricted | Built 2020 - 2022 | 219 homes
Regency at Creekside
$900Ks
Regency at Creekside, Gainesville, VA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 208 homes
The Atrium at MetroWest
$700Ks
The Atrium at MetroWest, Fairfax, VA
New Construction | 55+ age-restricted | Built 2018 - present | 206 homes
Four Seasons at Virginia ...
$400Ks - $600Ks
Four Seasons at Virginia ..., Woodbridge, VA
New Construction | 55+ age-restricted | Built 2021 - present | 185 homes
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Central Parke at Lowes Is...
$400Ks - $700Ks
Central Parke at Lowes Is..., Sterling, VA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 181 homes
Summerlake
$300Ks
Summerlake, Fredericksburg, VA
Resale Only | 55+ age-restricted | Built 1987 - 1997 | 161 homes
Belmont Bay
$400Ks - $800Ks
Belmont Bay, Woodbridge, VA
New and Resale | Age-targeted | Built 2007 - present | 155 homes
Regency at Belmont
$900Ks
Regency at Belmont, Ashburn, VA
New Construction | 55+ age-restricted | Built 2021 - present | 145 homes
Spring Valley Estates
$300Ks
Spring Valley Estates, Waynesboro, PA
New Construction | 55+ age-restricted | Built 2019 - present | 140 homes
The Woodlands of Urbana 3225 THORNAPPLE DR, FREDERICK, MD, 21704, Frederick, MD 21704
$615,000

3 beds

|

3 baths

|

1,816 sq ft

3225 THORNAPPLE DR, FREDERICK, MD, 21704
Signature Club at Greenview 5810 WHITEROSE WAY, NEW MARKET, MD, 2177..., New Market, MD 21774
$459,900

3 beds

|

4 baths

|

2,410 sq ft

5810 WHITEROSE WAY, NEW MARKET, MD, 2177...
Gatherings at Cabin Branch 13240 PETREL ST # 5203, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$610,990

3 beds

|

2 baths

|

1,887 sq ft

|

Condo

13240 PETREL ST # 5203, CLARKSBURG, MD, ...
The Village at Cabin Branch 13240 PETREL ST # 5203, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$610,990

3 beds

|

2 baths

|

1,887 sq ft

|

Condo

13240 PETREL ST # 5203, CLARKSBURG, MD, ...
The Village at Cabin Branch 13240 PETREL ST # 5207, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$615,990

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13240 PETREL ST # 5207, CLARKSBURG, MD, ...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Gatherings at Cabin Branch 13240 PETREL ST # 5207, CLARKSBURG, MD, ..., Clarksburg, MD 20871
$615,990

3 beds

|

2 baths

|

2,031 sq ft

|

Condo

13240 PETREL ST # 5207, CLARKSBURG, MD, ...
Gatherings at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
The Village at Cabin Branch 13240 PETREL ST # 106, CLARKSBURG, MD, 2..., Clarksburg, MD 20871
$399,990

1 beds

|

1 baths

|

1,203 sq ft

|

Condo

13240 PETREL ST # 106, CLARKSBURG, MD, 2...
Courts of Clarksburg 21822 BONESET WAY, GERMANTOWN, MD, 20876, Germantown, MD 20876
$643,000

3 beds

|

2 baths

|

1,540 sq ft

21822 BONESET WAY, GERMANTOWN, MD, 20876
The Village at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$479,900

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Gatherings at Cabin Branch 13504 GOLDENEYE CIR, CLARKSBURG, MD, 208..., Clarksburg, MD 20871
$479,900

3 beds

|

3 baths

|

1,590 sq ft

13504 GOLDENEYE CIR, CLARKSBURG, MD, 208...
The Village at Foxfield 1 KELLER LN, MIDDLETOWN, MD, 21769, Middletown, MD 21769
$574,900

3 beds

|

3 baths

|

3,161 sq ft

1 KELLER LN, MIDDLETOWN, MD, 21769
Gatherings at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
The Village at Cabin Branch 13444 PETREL ST, CLARKSBURG, MD, 20871, Clarksburg, MD 20871
$564,999

3 beds

|

3 baths

|

1,933 sq ft

13444 PETREL ST, CLARKSBURG, MD, 20871
The Woodlands of Urbana 2928 HERB GARDEN DR, FREDERICK, MD, 2170..., Frederick, MD 21704
$725,000

3 beds

|

4 baths

|

3,634 sq ft

2928 HERB GARDEN DR, FREDERICK, MD, 2170...
Want to learn more about 55+ communities in Winchester? 55places can help!
Questions? Call us: (540) 773-2470
Emerald Pointe 19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742, Hagerstown, MD 21742
$359,900

2 beds

|

2 baths

|

1,834 sq ft

19446 SAPPHIRE DR, HAGERSTOWN, MD, 21742
Community: Emerald Pointe
Emerald Pointe 13430 MARQUISE DR # 80, HAGERSTOWN, MD, ..., Hagerstown, MD 21742
$429,000

2 beds

|

3 baths

|

2,739 sq ft

13430 MARQUISE DR # 80, HAGERSTOWN, MD, ...
Community: Emerald Pointe
Emerald Pointe 19554 TURQUOISE DR V219, HAGERSTOWN, MD,..., Hagerstown, MD 21742
$484,900

2 beds

|

2 baths

19554 TURQUOISE DR V219, HAGERSTOWN, MD,...
Community: Emerald Pointe

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258 homes near Winchester
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